JPS6353856B2 - - Google Patents
Info
- Publication number
- JPS6353856B2 JPS6353856B2 JP59035321A JP3532184A JPS6353856B2 JP S6353856 B2 JPS6353856 B2 JP S6353856B2 JP 59035321 A JP59035321 A JP 59035321A JP 3532184 A JP3532184 A JP 3532184A JP S6353856 B2 JPS6353856 B2 JP S6353856B2
- Authority
- JP
- Japan
- Prior art keywords
- pfcp
- catalyst
- chromium
- oxidation
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000003054 catalyst Substances 0.000 claims description 28
- 239000011651 chromium Substances 0.000 claims description 24
- 238000007254 oxidation reaction Methods 0.000 claims description 18
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052804 chromium Inorganic materials 0.000 claims description 14
- 230000003647 oxidation Effects 0.000 claims description 14
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 claims description 11
- LTVOKYUPTHZZQH-UHFFFAOYSA-N difluoromethane Chemical group F[C]F LTVOKYUPTHZZQH-UHFFFAOYSA-N 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 229910052684 Cerium Inorganic materials 0.000 claims description 5
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 3
- 208000037550 Primary familial polycythemia Diseases 0.000 description 27
- 208000017693 primary familial polycythemia due to EPO receptor mutation Diseases 0.000 description 27
- 239000007800 oxidant agent Substances 0.000 description 10
- 150000002576 ketones Chemical class 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 238000005342 ion exchange Methods 0.000 description 6
- -1 difluoromethylene sulfonate Chemical compound 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003333 secondary alcohols Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical compound FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VGRZISGVNOKTQU-UHFFFAOYSA-N 4-(hydroxymethyl)cyclohexan-1-ol Chemical compound OCC1CCC(O)CC1 VGRZISGVNOKTQU-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- HFJRKMMYBMWEAD-UHFFFAOYSA-N dodecanal Chemical compound CCCCCCCCCCCC=O HFJRKMMYBMWEAD-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000003138 primary alcohols Chemical class 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- OOFMPQZBFAZZBO-UHFFFAOYSA-N undecane-1,10-diol Chemical compound CC(O)CCCCCCCCCO OOFMPQZBFAZZBO-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- HNTAJRDNEDXPDP-CSKARUKUSA-N (2e)-cyclododec-2-en-1-ol Chemical compound OC/1CCCCCCCCC\C=C\1 HNTAJRDNEDXPDP-CSKARUKUSA-N 0.000 description 1
- 229910000667 (NH4)2Ce(NO3)6 Inorganic materials 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ODSQCHUEHAGMIH-UHFFFAOYSA-N 1-ethenoxy-2-ethoxypropane Chemical compound CCOC(C)COC=C ODSQCHUEHAGMIH-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- IACCVEKYDYBVMH-UHFFFAOYSA-N 11-hydroxyundecan-2-one Chemical compound CC(=O)CCCCCCCCCO IACCVEKYDYBVMH-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- KHMBXNKCMNGLKG-UHFFFAOYSA-N 4-(hydroxymethyl)cyclohexan-1-one Chemical compound OCC1CCC(=O)CC1 KHMBXNKCMNGLKG-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001768 cations Chemical group 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- OBTWBSRJZRCYQV-UHFFFAOYSA-N sulfuryl difluoride Chemical group FS(F)(=O)=O OBTWBSRJZRCYQV-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- XMUJIPOFTAHSOK-UHFFFAOYSA-N undecan-2-ol Natural products CCCCCCCCCC(C)O XMUJIPOFTAHSOK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/16—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation
- C07C51/285—Preparation of carboxylic acids or their salts, halides or anhydrides by oxidation with peroxy-compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/06—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides containing polymers
- B01J31/08—Ion-exchange resins
- B01J31/10—Ion-exchange resins sulfonated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/30—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59035321A JPS60179148A (ja) | 1984-02-28 | 1984-02-28 | ペルフルオロカ−ボンポリマ−酸化触媒およびカルボニル化合物の製造方法 |
| US06/700,655 US4618724A (en) | 1984-02-28 | 1985-02-11 | Perfluorocarbon polymer oxidation catalyst and preparation of carbonyl compound |
| US06/765,151 US4617153A (en) | 1984-02-28 | 1985-09-17 | Perfluorocarbon polymer oxidation catalyst and preparation of carbonyl compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59035321A JPS60179148A (ja) | 1984-02-28 | 1984-02-28 | ペルフルオロカ−ボンポリマ−酸化触媒およびカルボニル化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60179148A JPS60179148A (ja) | 1985-09-13 |
| JPS6353856B2 true JPS6353856B2 (enExample) | 1988-10-25 |
Family
ID=12438545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59035321A Granted JPS60179148A (ja) | 1984-02-28 | 1984-02-28 | ペルフルオロカ−ボンポリマ−酸化触媒およびカルボニル化合物の製造方法 |
Country Status (2)
| Country | Link |
|---|---|
| US (2) | US4618724A (enExample) |
| JP (1) | JPS60179148A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3389176B2 (ja) * | 1999-11-17 | 2003-03-24 | 科学技術振興事業団 | 高分子担持ルイス酸触媒 |
| CN105985274B (zh) * | 2015-01-30 | 2017-11-07 | 中国科学院上海有机化学研究所 | 二氟甲基取代的硫代芳基磺酸酯、其制备方法及应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB626048A (en) * | 1944-10-01 | 1949-07-08 | Ladislaw Vilmos Farkas | A process of oxidizing primary or secondary alcoholic hydroxyl groups and aldehyde groups |
| US2861045A (en) * | 1954-11-15 | 1958-11-18 | Exxon Research Engineering Co | Catalytic metal-modified resin |
| US3840566A (en) * | 1972-06-15 | 1974-10-08 | Ventron Corp | Oxidation of primary alcohols |
| US4179403A (en) * | 1977-12-19 | 1979-12-18 | Shell Oil Company | Resin-ligand-metal complex compositions |
| US4338269A (en) * | 1980-12-05 | 1982-07-06 | Panelgraphic Corporation | Method of forming an abrasion-resistant coating on molded articles |
| US4426534A (en) * | 1981-09-22 | 1984-01-17 | Thiokol Corporation | Method for producing aldehydes and ketones using 2,2'-bipyridinium chlorochromate as oxidizing agent |
| IT1152298B (it) * | 1982-07-28 | 1986-12-31 | Anic Spa | Procedimento per l'ossidazione di alcooli ad aldeidi e/o chetoni |
| US4438269A (en) * | 1982-08-09 | 1984-03-20 | Thiokol Corporation | 4-Dimethylaminopyridinium chlorochromate |
-
1984
- 1984-02-28 JP JP59035321A patent/JPS60179148A/ja active Granted
-
1985
- 1985-02-11 US US06/700,655 patent/US4618724A/en not_active Expired - Fee Related
- 1985-09-17 US US06/765,151 patent/US4617153A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4618724A (en) | 1986-10-21 |
| JPS60179148A (ja) | 1985-09-13 |
| US4617153A (en) | 1986-10-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW201038518A (en) | Process for producing phenol | |
| JPS6353856B2 (enExample) | ||
| CN102452918B (zh) | 一种催化氧化羟基酸制备相应二元羧酸的方法 | |
| CN100513376C (zh) | 己二酸的制备方法 | |
| JP2000103758A (ja) | 芳香族ケトンの製造方法 | |
| US4115440A (en) | Selenium catalyzed decomposition of peroxide intermediates resulting from the autoxidation of acrolein and methacrolein | |
| JPH11349560A (ja) | 過酸化合物の製造方法 | |
| CN116693453A (zh) | 一种催化氧化制备二氯喹啉酸的新工艺 | |
| KR100965633B1 (ko) | 물에서 ｐ-크실렌의 액상 산화에 의한 ｐ-톨루엔산의제조방법 | |
| JP4601805B2 (ja) | シクロヘキサンの酸化方法 | |
| CN116640047A (zh) | 4-羟基联苯的制备方法 | |
| CN110423185B (zh) | 一种异丙苯类化合物选择性氧化的方法 | |
| JP2003113131A (ja) | アルコール類の新規酸化法 | |
| US5608106A (en) | Preparation of alkoxyalkanoic acids | |
| JP2004524296A (ja) | 酸化触媒としての安定なフリーニトロキシルラジカル及び酸化方法 | |
| CN1317250C (zh) | 羰基化合物的制备方法 | |
| EP1184076B1 (en) | Polymer-supported lewis acid catalyst | |
| RU2365576C1 (ru) | Способ получения 2-метил-1,4-нафтохинона | |
| JPS6345666B2 (enExample) | ||
| JP3968427B2 (ja) | カルボン酸の製造方法 | |
| JP2521079B2 (ja) | 粘弾性体を用いる反応方法 | |
| US4565895A (en) | Process for the preparation of 4-hydroxy-2,4,6-trimethyl-2,5-cyclohexadienone | |
| CA1253884A (en) | Process for producing 2,6-naphthalenediol | |
| CN116715568A (zh) | 一种对二乙苯衍生物的绿色合成方法及其催化剂及应用 | |
| JPH03101672A (ja) | ２，５―フランジカルボキシアルデヒドの製法 |